Sulfuric Acid → Hexanoic acid, 6-hydroxy-, methyl ester

ε-Caprolactone (12.50 g, 109.51 mM) was dissolved in methanol (125 ml), and a sulfuric acid solution (1 ml, 0.01 mM) was slowly added thereto. The resulting mixture was stirred at room temperature for 2 days. After the completion of reaction, methanol was removed under reduced pressure, and then ice water was poured into the residue. The resulting mixture was extracted with ethyl ether. The organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and brine in order and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to obtain 10.18 g of the title compound (yield 64%).

1. customwas removed under reduced pressure
2. additionice water was poured into the residue
3. extractionThe resulting mixture was extracted with ethyl ether
4. customThe organic layer was separated
5. washwashed with an aqueous saturated sodium bicarbonate solution and brine in order
6. concentrationconcentrated under reduced pressure
7. customThe residue thus obtained

ORD record

ord-f043808d3e60469ebbad9e3eacb5dae8

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08053435B2